Maleimide
(Synonyms: 马来酰亚胺) 目录号 : GC38288
Maleimide exhibits fluorescence quenching ability and can be used for the specific detection of thiol analytes as fluorogenic probes. Maleimide is also used for production of antibody-drug conjugate (ADC) which is used in cancer research.
Cas No.:541-59-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Maleimide exhibits fluorescence quenching ability and can be used for the specific detection of thiol analytes as fluorogenic probes. Maleimide is also used for production of antibody-drug conjugate (ADC) which is used in cancer research.
[1] Kévin Renault, et al. Bioconjug Chem. 2018 Aug 15;29(8):2497-2513.
| Cas No. | 541-59-3 | SDF | |
| 别名 | 马来酰亚胺 | ||
| Canonical SMILES | O=C(N1)C=CC1=O | ||
| 分子式 | C4H3NO2 | 分子量 | 97.07 |
| 溶解度 | DMSO: ≥ 100 mg/mL (1030.18 mM); Water: 50 mg/mL (515.09 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 10.3018 mL | 51.5092 mL | 103.0184 mL |
| 5 mM | 2.0604 mL | 10.3018 mL | 20.6037 mL |
| 10 mM | 1.0302 mL | 5.1509 mL | 10.3018 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Maleimide structure: a promising scaffold for the development of antimicrobial agents
J Asian Nat Prod Res 2022 Jan;24(1):1-14.PMID:33511872DOI:10.1080/10286020.2021.1877675.
Natural compounds bearing Maleimide rings are a series of secondary metabolites derived from fungi/marine microorganisms, which are characterized by a general structure -CO-N(R)-CO-, and the R group is normally substituted with alkyl or aryl groups. Maleimide compounds show various biological activities such as antibacterial, antifungal, and anticancer activity. In this review, the broad-spectrum antimicrobial activities of 15 Maleimide compounds from natural sources and 32 artificially synthesized maleimides were summarized, especially against Candida albicans, Sclerotinia sclerotiorum, and Staphylococcus aureus. It highlights that Maleimide scaffold has tremendous potential to be utilized in the development of novel antimicrobial agents.
Maleimide-based method for elaboration of cysteine-containing peptide phage libraries
Methods Mol Biol 2015;1248:267-76.PMID:25616339DOI:10.1007/978-1-4939-2020-4_18.
Peptide-based molecules are known to have therapeutic utility, but the generation of phage-focused libraries to optimize peptide properties and functionality is challenging. Genetic approaches are limited to peptide extension on the peptide termini. Current chemical methods are technically challenging and time-consuming. A new chemical method is developed to extend a maleimide-conjugated peptide with a cysteine-containing random peptide phage display library. As a proof of concept, a 15-mer epidermal growth factor receptor (EGFR)-binding peptide was synthesized with a Maleimide group at its C-terminus and then conjugated to the cysteine-containing library. After panning and screening, several extended peptides were discovered and tested to have a higher affinity to EGFR. This strategy can have broad utility to optimize pharmacophores of any modalities (peptides, unnatural peptides, drug conjugates) capable of bearing a Maleimide group.
Maleimide-functionalized photochromic spirodihydroindolizines
J Org Chem 2013 Mar 1;78(5):1903-9.PMID:23095100DOI:10.1021/jo301894s.
Two photochromic spirodihydroindolizine/betaine systems for tethering to peptides and proteins via a Maleimide function have been prepared. The absorption spectra of the betaines are in the red region of the visible spectrum and in the near-IR spectral domain, which are suitable energies of light for future in vivo applications. The half-times of cyclization have been determined for both DHI/betaine systems. The findings are consistent with a thermal barrier of varying size between the transoid and cisoid conformers of the betaines.
Maleimide-functionalized carboxymethyl cellulose: A novel mucoadhesive polymer for transmucosal drug delivery
Carbohydr Polym 2022 Jul 15;288:119368.PMID:35450630DOI:10.1016/j.carbpol.2022.119368.
The objective of this research was to develop a novel mucoadhesive polymer for drug delivery applications based on N-(2-aminoethyl) maleimide-functionalized carboxymethyl cellulose in which the weight ratios of the materials were tuned to explore the condition providing the highest Maleimide content on the polymer. The polymers were synthesized from N-(2-aminoethyl) Maleimide that was conjugated to carboxymethyl cellulose with their mucoadhesive properties examined by tensile testing, rheology, and flow-through analysis and their biocompatibilities evaluated on the human gingival fibroblast cell line (HGF-1). The anti-inflammatory drug benzydamine was loaded into mucoadhesive-polymer-based tablets and used to demonstrate the application of the synthesized polymer. The polymer exhibited superior mucoadhesive capability compared to carboxymethyl cellulose through the interaction between Maleimide moiety and mucin. The functionalized polymer also possessed the ability to control the release of benzydamine with Higuchi's release model and was proven to be a potential candidate in mucoadhesive drug delivery.
Covalent Modification of Biomolecules through Maleimide-Based Labeling Strategies
Bioconjug Chem 2018 Aug 15;29(8):2497-2513.PMID:29954169DOI:10.1021/acs.bioconjchem.8b00252.
Since their first use in bioconjugation more than 50 years ago, maleimides have become privileged chemical partners for the site-selective modification of proteins via thio-Michael addition of biothiols and, to a lesser extent, via Diels-Alder (DA) reactions with biocompatible dienes. Prominent examples include immunotoxins and marketed maleimide-based antibody-drug conjugates (ADCs) such as Adcetris, which are used in cancer therapies. Among the key factors in the success of these groups is the availability of several maleimides that can be N-functionalized by fluorophores, affinity tags, spin labels, and pharmacophores, as well as their unique reactivities in terms of selectivity and kinetics. However, Maleimide conjugate reactions have long been considered irreversible, and only recently have systematic studies regarding their reversibility and stability toward hydrolysis been reported. This review provides an overview of the diverse applications for maleimides in bioconjugation, highlighting their strengths and weaknesses, which are being overcome by recent strategies. Finally, the fluorescence quenching ability of maleimides was leveraged for the preparation of fluorogenic probes, which are mainly used for the specific detection of thiol analytes. A summary of the reported structures, their photophysical features, and their relative efficiencies is discussed in the last part of the review.